Winter Haven is a golfer's town. Willowbrook Golf Course is a popular option for visitors, and the Country Club of Winter Haven is one of Central Florida's most historic private clubs, with roots going back to 1923. Courses here wind alongside lakes and through natural Florida landscape — which means you're likely to share the fairway with a few ospreys and great blue herons whether you want to or not.
Whether you prefer kayaking, paddleboarding, or a relaxing scenic boat tour, the Chain of Lakes has something for everyone. Guided pontoon cruises are a wonderful way to take it all in without breaking a sweat. Fishing is excellent year-round, and sunset on the water here is simply something you have to experience to believe.
Historic Downtown Winter Haven is a vibrant hub of unique shops, local dining, and art galleries showcasing works from local and regional artists.
It's the kind of downtown that rewards a slow stroll — grab a coffee, browse the boutiques, and settle in for a meal somewhere with a view of the lake.
Circle B Bar Reserve is a standout destination for birdwatching and hiking and is beloved by nature enthusiasts from around the country. Winter Haven's network of parks — including South Lake Howard Nature Park and Lake Hartridge Nature Park — offers peaceful walking trails, birding spots, and quiet lakeside settings perfect for an easy morning out.
The Winter Haven area has quietly developed a genuine craft beer culture, and for those who enjoy a well-made pint in a relaxed, social atmosphere, there's plenty to explore right in the neighborhood.
Grove Roots Brewing Co
Swan Brewing — Lakeland
Just south of us in Lake Wales, Bok Tower Gardens is a 250-acre contemplative garden and bird sanctuary. This is one of those places that quietly takes your breath away.
At the heart of the gardens stands the iconic Singing Tower, whose 60-bell carillon fills the air with music during daily concerts — a peaceful and unforgettable experience.
LEGOLAND Florida Resort is a 150-acre interactive theme park built specifically for families with children between the ages of 2 and 12, with more than 50 rides, shows, and attractions. his isn't a park you rush through — between the LEGO Movie ride, the NINJAGO ride, The Dragon roller coaster, the water park, and the hands-on building zones, kids could easily fill two full days here and still find something new. It's right here in Winter Haven, just a short drive from our front gate.
Peppa Pig Theme Park is a standalone theme park just steps away from LEGOLAND Florida Resort Expedia, making it easy to combine both in one trip. Designed especially for the toddler and preschool crowd, it features gentle rides, live shows, and the now-famous muddy puddle splash area that younger grandchildren absolutely lose their minds over. If you've got little ones under 6, this is their park.
Andy's Drive-In has been serving Winter Haven since 1951, and is beloved for its Steakette Burger and its Fruit Salad Milkshake — packed with fresh peaches, pineapple, cherries, and bananas — with a Sunday walk-up ice cream window offering 20 flavors. TRIP.COM The prices are old-school casual and the atmosphere is pure Americana. Kids love it. Grandparents love it. It's just one of those places.
Winter Haven sits about 30 miles from Walt Disney World and roughly 45 minutes from Universal Studios. For the grandkids who are begging for the big parks, you've got easy access — but the great thing about being based here is that you come home to peace and quiet instead of a crowded Orlando hotel. You get the best of both worlds.
About 20 minutes away in Lakeland, the Florida Children's Museum offers hands-on, interactive exhibits — from an art studio to a pretend doctor's office — designed to spark creativity, exploration, and curiosity in kids of all ages. NorthPennNow A perfect rainy morning option, and a nice change of pace from the theme park experience.
When the afternoon Florida thunderstorm rolls in (and it will), Incredibowl Entertainment in Winter Haven is an indoor wonderland packed with bowling, laser tag, arcade games, and obstacle courses — something for every age and energy level. NorthPennNow Affordable, air-conditioned, and genuinely fun for grandparents and grandkids alike.
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